Paul is a problem sometimes. Like, for instance, he says, "If possible so far as it depends on you, be at peace with all" (Romans 12:18) and then he goes and writes something like this:
Women should adorn themselves in respectable apparel, with modesty and self-control, not with braided hair and gold or pearls or costly attire, but with what is proper for women who profess godliness—with good works. (1 Timothy 2:9-10)
Paul, Paul, what were you thinking, man? You can't get away with something like that? Don't you know this will cause no end of conflict between men and women, no end of "no peace"? Really, Paul. You can't tell women how to dress.
It wasn't that long ago that the standard of modesty for women was "no ankle showing." I admit, that was before my time, but it wasn't a lot before my time. As the years went by, the skirt length requirement rose. From "show some ankle" to "perhaps the calves" to my day when it was "at the knees" (and they'd make girls kneel to make sure the hem touched the ground). After that there was no stopping it. "Six inches above the knee" to today's version that says, "No genitals showing" (seriously).
Now, tell me again, what is "modesty"? We're not entirely sure anymore, but we're pretty sure Paul has no place calling for it.
The dictionary defines modesty as "regard for decency of behavior, speech, dress, etc." (among other things, of course). The first thought (at least among conservative Christians) is "not showing too much skin; not creating sexual arousal." I guess that would fall under "regard for decency," but that's certainly not all. Paul uses the same word in 1 Timothy 3:2 where elders are required, among other things, to be "respectable," so it's not a "woman thing." If biblical "modesty" is also "respectable" (the word is kosmios meaning "orderly, of good behavior, seemly"), then what is Paul talking about in that text?
First, we acknowledge that it is an issue for both males and females. So, if we are to all be "modest" and not merely "not showing too much skin," what is that? It is to be respectable, to be orderly, to be seemly. It speaks of conforming to propriety. We need to consider "What is appropriate?" If we answer that question from Scripture, we end up somewhere we may not have considered. Paul said we should, "Do nothing from selfish ambition or conceit, but in humility count others as more significant than yourselves. Let each of you look not only to his own interests, but also to the interests of others" (Philippians 2:3-4). That, Paul suggests, is seemly -- appropriate. Like Christ (Philippians 2:5).
Where does that take us? If we are to be kosmios, we should be humble, considering others first. As such, our question in dress and behavior would not be "What would make me look best?" but "What would be best for others?" Women and men should dress with that in mind, act with that in mind, speak with that in mind. That is modesty. That is the aim. Biblical modesty speaks of propriety -- what is appropriate -- and and what is biblically appropriate is "Love God" and "Love your neighbor." If you let that drive how you dress and act and speak and live, you will do well. Hmm, perhaps Paul was not completely crazy.
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